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Ambident reactivity of 5-aminopyrazoles towards donor–acceptor cyclopropanes Full article

Journal Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539
Output data Year: 2022, Volume: 20, Number: 39, Pages: 7795-7802 Pages count : 8 DOI: 10.1039/d2ob01490d
Authors Vartanova Anna E 1 , Levina Irina I. 2 , Ratmanova Nina K. 3,1 , Andreev Ivan A. 3,1 , Ivanova Olga A 4,1 , Trushkov Igor V. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, Moscow 119334, Russian Federation
2 N. M. Emanuel Institute of Biochemical Physics Russian Academy of Sciences, Kosygina 4, Moscow 119334, Russian Federation
3 Dmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela 1, Moscow 117997, Russian Federation
4 Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow, Russian Federation

Abstract: Lewis acid-catalysed reactions of donor–acceptor cyclopropanes with 1,3-disubstituted 5-aminopyrazoles were investigated. Under catalysis with gallium(III) chloride, products of the three-membered ring opening via a nucleophilic attack of the exocyclic amino group were obtained in a chemoselective manner. Oppositely, in the presence of scandium(III) triflate, products of either N-alkylation or C(4)-alkylation, or a mixture of both were formed. The products of the C(4) alkylation were transformed in one step into tetrahydropyrazolo[3,4-b]azepines that are attractive for medicinal chemistry and pharmacology.
Cite: Vartanova A.E. , Levina I.I. , Ratmanova N.K. , Andreev I.A. , Ivanova O.A. , Trushkov I.V.
Ambident reactivity of 5-aminopyrazoles towards donor–acceptor cyclopropanes
Organic & Biomolecular Chemistry. 2022. V.20. N39. P.7795-7802. DOI: 10.1039/d2ob01490d WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000857166900001
Scopus: 2-s2.0-85139739789
OpenAlex: W4295938091
Citing:
DB Citing
OpenAlex 9
Scopus 8
Web of science 7
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